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Thiessen grew up on the Upper East Side in Manhattan, where both his parents were doctors and "left-of-center liberal Democrat types."[2] His mother grew up in Poland and fought as a teenager in the Warsaw Uprising, a military struggle in which his grandfather died.[2]

Thiessen has worked in Washington for many years, starting with five years at Black, Manafort, Stone and Kelly. He spent six years (1995–2001) on Capitol Hill as spokesman and senior policy advisor to Senate Foreign Relations Committee Chairman Jesse Helms (R-NC).[3] He joined the Bush administration as Chief Speechwriter for Donald Rumsfeld in 2001, then moved to Bush's speechwriting team in 2004.[3] In February 2008, he became chief speechwriter when William McGurn resigned. [4]

Jane Mayer, author of The Dark Side: The Inside Story of How The War on Terror Turned into a War on American Ideals, a book which Thiessen says has fundamental errors of fact,[13] heavily criticized Courting Disaster in a book review, claiming it is "based on a series of slipshod premises."[14] In a long response, Thiessen defended the accuracy of his book and said Mayer's review contained many factual errors and omissions. For example, Mayer quoted the head of Scotland Yard's anti-terrorism branch in 2006 as saying that Thiessen's account of the Heathrow plot is "completely and utterly wrong";[14] in reply Thiessen quoted a former senior CIA official as saying that the CIA liaises only with MI6 and MI5, so the Scotland Yard official "would have no way of knowing what intelligence the CIA shared with MI6 or MI5, much less the ultimate source of that intelligence". Thiessen added, "The week her article appeared in The New Yorker, former CIA director Mike Hayden handed it out in his class at George Mason University's School of Public Policy as an example of all that is wrong with intelligence journalism today."[15]